The moment Dave Kashen hops on a Zoom with me, there seems to be a palpable shift in energy — a good one. He greets me with an ear-to-ear smile and tells me the source of it before I can even ask. “I’m feeling really energized. I did a couple of Tony Robbins events in the last couple of weeks, and it’s been quite an expansive year,” he says, beaming. “I also did the Hoffman process — you know what that is?”

I nod. I didn’t, in fact, know what it was until a few days earlier when I did a deep dive into Kashen’s work as a conscious leadership coach (and former 2x startup founder), stitching together snippets of information to create a mental collage of Kashen — who has worked with clients including Nir Eyal (best-selling author of Hooked), Mike Krieger (co-founder and CTO of Instagram), and Alex Lieberman (co-founder of Morning Brew) — ahead of our call.

The Hoffman Process, I learned, is a week-long growth retreat founded back in 1967 that aims to help participants identify and build consciousness around negative behaviors that may have developed unconsciously at some point in their lives — such that they can break the patterns and shift to a more positive way of living.

“I feel really expanded,” Kashen says, reflecting on the process. “And I love that it’s sort of double duty for me when I do these things because I get all this growth and insight, and then I’m able to immediately share it and bring it to clients.”

It’s clear hearing you talk about your work that this is what you’re meant to do. But it’s not where you started out, right?

I grew up on Long Island with lots of messages around money and status and success, and I focused on that — I got good grades, went to Wharton, studied finance, went to work at Goldman Sachs. Then I moved from New York out to the Bay area to work for one of the best-performing hedge funds of all time, a fund called SPO Partners.

And I was like, "I've arrived," you know. It was the job I thought I was always supposed to want — but I found myself utterly unfulfilled.

It just wasn’t what you expected.

It was like, I climbed to the top of this mountain where I was told this gold would be — in terms of inner peace and fulfillment — and it wasn't there. My hypothesis was that creating something in the world that improved people's lives would be more fulfilling.

I know you went on to found online health and wellness company Wellsphere, your first of two companies. So you felt this purpose to serve others, but you still hadn’t translated that to coaching just yet?

Yeah. To be honest, my co-founder and I — our values weren’t fully aligned. And I really suffered for that four-year journey because it just wasn't true to who I was. Eventually, when we got acquired, I was like, “Okay, I can finally step back a little bit.” That’s when I hired a coach for myself for the first time, and he encouraged me to go to a program called The Landmark Forum, where they help you distinguish what happened in your life from the stories you tell yourself about what happened. That created the possibility of living a more authentic life, which I realized, for me, meant helping other humans thrive and awaken to the truth of who they are so they can live from that place.

So you had this kind of eye-opening experience, and this is where the idea to start coaching set in. What did you do next?

I quit. And to be fair, I was super scared. I was recently married, we had our first child, and most (or at least a lot) of the deal economics of the acquisition were in the retention — it was a one-year retention package. I quit about six months in and everyone thought I was crazy. I was trembling and called the CEO — this wonderful guy, Chris Schroeder, who ran the company that acquired us. I said, “Hey, I know what I'm here on earth to do. I gotta go do it.”

Wow. What was his response to that?

He ended up hiring me as his coach.

It’s interesting to hear you talk about it because, on one hand, you seem to have had such resolve that this is what you were meant to be doing, but on the other hand, there was still this fear that seemed to be creeping in.

We are wired for threat. Unless we achieve sort of Buddha-level enlightenment, we’ll always be bouncing back and forth between these different states.

Right. It’s like you have to just keep moving forward and trust that things will be okay to an extent.

My current view is that we don't live in a benevolent universe or a malevolent universe. We live in a mirroring universe. It basically means that the universe or reality mirrors our beliefs. And there's science around the reticular activating system and the way that our brains can't experience all of reality — we experience the part of reality that we focus on through the lens through which we perceive it. And so, from my experience, we perceive what we believe, not the other way around. So, I choose to believe that the universe is here to support my growth and learning. And by choosing to believe that, I experience it. And to me, it's an upward spiral where the more I look for how that's true, the more I experience it.

This all dovetails into the idea of conscious leadership, which is how you approach coaching. Can you tell me a bit more about this framework?

For the first five years of coaching, I was synthesizing all these different frameworks and methodologies. And then when I discovered conscious leadership, it so deeply resonated. It felt like a packaging of ancient wisdom into a very tangible set of principles, commitments, practices, and tools. The core of it is this distinction between content and context — if your life is a movie, what’s on the screen is the content, and the lens through which you see it is the context — and between states of being “below the line or “above the line.”

Below the line being a state of threat, and above the line being a state of trust?

Right. If we use different words, it’s the distinction between a victim and a creator. The creator takes responsibility for their experience. And responsibility does not mean self-blame, that's a common misconception. It means seeing yourself as the creator of your experience.

You’ve talked about this before, but I think a big part of being able to enter that state of consciousness comes down to our relationship with our egos, right? Our egos are these kinds of characters in our story that sort of interfere with that sense of conscious clarity.

Right. There's this term I heard or read somewhere called "selfing." It actually takes effort to create the notion of self. Like if you really get curious and look at the experience of life, all that's ever actually occurring is this knife-edge intersection between the present moment and our consciousness. And the notion of self — this Dave character who has been an entrepreneur, and has friends and family, and all these different traits — that is actually an invention of mind. It requires mental effort to invent this image of this persistent Dave character. And I think the trap of the ego is that we build that image, we believe that's who we are, and then we spend a lot of energy on aggrandizing and protecting that image we have of self. That’s why, if I get an email from a client saying they’re thinking of pausing coaching, I might jump to “Maybe I’m not as good a coach as I thought.” We go into this state of threat and make it personal and a reflection of our self-image rather than just experiencing life as it is in the present moment.

How do you see that come up with a lot of your coaching clients in the startup space?

One of the biggest breakthroughs most of my entrepreneur clients have is when I ask them different forms of the question: “Are you willing to let go of attachment to your company being successful? Are you willing to see how your company failing could be as good or better than your company being successful?” And many of them respond no fucking way.

It’s like you said before, that sense of self for founders is so often intertwined with the company they’re building. I imagine that’s a really prominent pattern in how the ego shows up for a lot of your startup clients.

Right, there’s this fusing of identity and their sense of significance or worthiness with the success of the company. That has a huge impact on a human being when you believe that your worthiness depends on your company's success. That's the core fear of every human — that we’re not worthy or lovable or enough. But it gets exaggerated as a startup founder because it's so public and you can’t detach your identity from the company as easily as an employee can, for example.

But another pattern I see is founders taking more than 100% responsibility for their investors and team. Like, "I have to make sure my investors make money. I have to make sure my team has a job." And I often challenge founders. I ask them: What have you actually committed to? Do you believe your investors think that you've guaranteed them a return? Or is it that they believe that you've committed to giving it your all? Often, that can be a release. But our ego minds are obsessed with being right. We want to be right that investors making money and that the team keeping their jobs is the "good" outcome, and that investors losing money and team members losing jobs is the "bad" outcome. But I challenge clients to think about how the opposite could be true, just like I said before with the question of how a company failing could be just as good or better than it succeeding. In this case, how could investors losing money on this investment be just as good or better for them? How could team members losing their jobs be just as good or better?

It’s not that I want them to fail, or lose investors’ money, or have to fire people.  It turns out that, paradoxically, the less attached you are to an outcome, the easier — and more joyful — it is to create.

It’s interesting because I think there’s a lot about startups that is so heavily rooted in proof, right? Proof of concept, proof of product-market fit, proof of growth. But as you’re talking, I’m also just thinking a lot about how founders are simultaneously trying to prove themselves.

I love to ask founders, what if you knew without a shadow of a doubt that you are already enough and worthy? And what comes up a lot is this distinction between being and doing. I think our society really collapses being and doing — as if who you are is simply the sum of your accomplishments. But when you can discern those two things, the “doing” can become much more like a game. And again, the less attached you are to the outcome, the easier it is to achieve and the easier is to gain clarity.

A lot of what we’re talking about here is quite conceptual. How do you think conscious leadership plays a role in informing more concrete business goals — revenue growth, fundraising success, etc. — in addition to supporting leaders’ personal growth and development?

The most common conversation I have with clients start with the day to day issues they’re facing: “Okay, my sales are not where I wanted them to be,” or “My VP of engineering is not performing the way I want,” or “I have this issue with my board,” this and that. And if we go back to the victim/creator distinction, the reason that any of these things is an issue is that they're "below the line" — in a state of threat — believing they're at the effect of something outside of them. So the first thing I do is go through the conscious leadership process:

• Awareness: "Where are you, above or below the line?" (By the way, if they're bringing up the issue, they're below the line, otherwise, they would have resolved it already.)
• Acceptance: "Can you accept yourself for being right where you are — yes or no?”
• Willingness to shift: “Are you willing to shift and take 100% responsibility for how you created it the way it is now?”

And one of my favorite tools is this tool called "write the recipe." If I wanted to miss sales by 40% the way you did, how would I create that experience? If I wanted to have conflict with my co-founder over the last two years, how would I create that experience? If I wanted to have a board that was critical and frustrating to me, how would I create that experience? If a client is willing to shift, they'll start to write the recipe and they'll literally see how they create this thing that they've been thinking was happening to them. Then it's just like, if you want to have a different experience, just do the opposite of all that.

And it might include beliefs, right? What must you believe about your board to be having this experience? “Oh, that they're the judge and jury of my worthiness.” Okay, well, can you let go of believing that? Or, “I've been frustrated, but I've been scared to have this hard conversation because we're about to raise money and I don't want to rock the boat.” Okay, well, at least you know how you're creating this experience. So I find if you're willing to take responsibility for how things are now, whatever they are, you can then see what there is to do to create what you want instead.

It kind of goes back to what you were saying about the benevolent universe.

Exactly. Can you shift from seeing this as happening to you, to happening for you? Are you willing to see this experience as an ally for your growth and learning? Like, okay, a key person quit, or you're running out of money — are you willing to see that as a worthy opponent? Something that's inviting you to be strong and resilient and creative? Or do you instead feel like, "Poor me, we're running out of money." To me, the whole startup journey is really about who you get to become through the process.

How would describe your relationship with your own ego today?

[It came up recently] in reflecting on how I prioritize certainty over love and contribution, which are three of the six core human needs that Tony Robbins talks about. Even though I’ve done all this work, still, in my programming and in my pattern was this need for certainty. And what that caused me to do was take on a lot of one-on-one clients even though I've had this instinct and this pull to have more scale of impact and want to serve more people. So after I did Hoffman, I was feeling courageous and I launched some new courses called the Inner Game of Entrepreneurship. And weeks into it, I had like one person signed up. I think within two weeks of the course, I had maybe three people signed up. And I went into my old patterns. Like, "Oh god, why did I do this? Coaching is so comfortable for me. Why did I have to go and create stress in my life, now I can't be present with my family because I'm all anxious and stressed and feeling like I need to hustle.” But I'm now also excited to face those same challenges and setbacks as a worthy opponent for me to grow and become able to be present even when I fail, or make a mistake, or things don't go well, instead of being constrained by needing to feel comfortable all the time.

It’s like you said: the startup journey — and every person’s journey, really — is just about who you get to become through the highs and lows of the process.

People are just these extraordinary beings of beauty and energy, but then there are all these layers of beliefs and patterns that get in the way of it. And so it's not even that we need to become something we're not already — it's that we need to remove all the beliefs and patterns that are in the way of us recognizing who we really are.